The synthesis of biaryl macrocyclic compounds containing highly strained 1,4-arene-bridged units, i.e., bent para-phenylenes, has recently emerged as an area of intense research investigation. Notable compounds containing these substructures include the haouamine alkaloids and the [n]cycloparaphenylenes (CPPs). Our group has recently employed a non-cross coupling-based approach, where an unstrained 1,4-diekto-bridge is converted into a strained 1,4-arene-bridge. The dehydrative aromatization of macrocyclic cyclohex-2-ene-1,4-diol precursors using the Burgess reagent, affords para-phenylene units that contain over 30 Kcal/mol of strain energy. Under these conditions no strain-induced rearrangement reactions occur.

Mild dehydrative aromatization protocol for accessing highly distorted para-phenylenes

251st National Meeting (2016)

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